The Midlife Chrysalis

What happens when success stops working and midlife hits hard? Blake Mycoskie, founder of TOMS Shoes, shares the story behind his most difficult chapter. After building a global brand and achieving massive success, Blake found himself facing a deep midlife reckoning marked by depression, loss of identity, and an urgent search for meaning beyond achievement. Blake opens up about: - How selling part...

What if aging alone isn’t the only option? As midlife reshapes relationships, identity, and housing, a bold question emerges: what if women chose community instead of solitude? In this Wisdom Wednesday episode, Chip Conley, founder of Modern Elder Academy, joins Derek Gehl to explore the early-stage idea behind Golden Girls–style living, an intentional housing experiment he’s beginning in Santa Fe...

Aging in America has never been the same for everyone. Chip Conley sits down with Ray Jetson , pastor, former Louisiana legislator, and author of Aging While Black , to explore why aging isn’t a race-neutral experience and what it really means to age well in a system that was never built for everyone. Ray shares a simple, powerful way to rethink aging through community, innovation, and shared wisd...

Most leaders are chasing short-term wins and missing the long game. In this episode, Chip Conley talks with Rand Stagen, founder of the Stagen Leadership Academy, about what’s quietly breaking leadership today and how to lead with purpose, perspective, and staying power. Rand shares hard-earned insights from decades of working with CEOs and entrepreneurs who want more than success, they want meani...

Most companies are racing toward AI, efficiency, and scale while quietly losing the one advantage that actually sustains great leadership: wisdom. In this Wisdom Wednesday episode, we reveal why culture, lived experience, and human judgment matter more than ever. Chip draws on decades of leadership experience to explain why many organizations are losing their edge and what they can do to reclaim i...

Have you ever reached a point in life where what once worked… suddenly doesn’t? In this warm conversation with Chip, Ben Katt, MEA’s faculty in residence and author of The Way Home, offers a hopeful reframe of midlife. Rather than seeing it as a breakdown, Ben invites us to see this season as a meaningful transition, one that asks us to let go of old roles and reconnect with who we truly are. In t...

What if the wellness advice you followed for years stops working after 50? In this episode, wellness pioneers Jeff Krasno, co-founder of Wanderlust, and Schuyler Grant, founder of Kula Yoga Project, share how their approach to health quietly but radically shifted in midlife, and why many popular wellness habits fall short as we age. With decades spent in yoga, wellness festivals, and lived experie...

Why most New Year’s resolutions fail before February? In this episode of Wisdom Wednesday, we take an honest look at why good intentions fade quickly and share a simple, practical framework for building habits that last. Drawing from real-life experience, we break down how to turn good intentions into daily actions, without relying on motivation alone. In this episode, you’ll learn: - Why most res...

Midlife can feel confusing, even when life looks good from the outside. Careers change, relationships shift, and the way we see ourselves starts to evolve, leaving many people feeling stuck in between what was and what’s next. In this episode, Kari Cardinale, Chief Content Officer and partner at Modern Elder Academy, explains why these moments aren’t breakdowns but transitions, and why learning to...

He didn’t plan on being successful. He just followed what pulled at him and kept letting go when it stopped working. In this episode, Stacy Peralta, legendary skateboarder, filmmaker behind Dogtown and Z-Boys, and modern elder, shares how a life built on passion, curiosity, and vulnerability led him from skateboarding to filmmaking to painting, without clinging to any single identity. Rather than...

In this Wisdom Wednesday episode, Chip Conley, entrepreneur, author, and founder of MEA, opens up about the quiet disappointment many high achievers feel after they’ve “made it.” Through stories from building iconic companies, guiding Airbnb’s founders, and navigating midlife reckoning, Chip explores the success treadmill, and why chasing the next win so often leaves us unsatisfied. In this conver...

What if the real risk in midlife isn’t change but staying comfortable? In this episode of Midlife Chrysalis, Chip Conley sits down with Dr. Margie Warrell, global expert on courage and bestselling author of The Courage Gap, to explore why so many smart, capable people feel stuck and how to move forward with clarity and bravery. Drawing from her journey from a rural Australian farm to the world sta...

Dating in midlife can feel strangely hard, even when you’ve done the work, built a full life, and know yourself better than ever. If you’ve ever thought, “Why is this still so complicated?” this episode is for you. In this conversation, I sit down with Rachel Greenwald, Harvard MBA and veteran matchmaker who has helped guide nearly 1,000 marriages. With warmth, humor, and deep insight, Rachel refr...

Feeling stuck in midlife? You might be in your chrysalis, not a crisis. In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation. Chip shares: • The three stages of every transition and where most people get stuck • What really happens inside the messy middle • Why men and wom...

What if midlife became your chance to ROAR, not retire? In this powerful conversation, bestselling author and longevity visionary Michael Clinton shares why your 40s, 50s, and beyond are actually the most exciting and opportunity-filled decades of your life. From his rise to the top of Hearst Magazines to running marathons on seven continents and earning a new degree at 67, Michael reveals how rei...

Ever wondered why some people get stronger, wiser, and more grounded with age? In this powerful conversation, Laird Hamilton and Gabby Reece reveal why midlife is actually the most dynamic, resilient, and liberating season of life. They open up about growing up on islands, how they met, what keeps their partnership strong, and why presence, patience, and community matter more than ever. From breat...

What if the secret to living longer isn’t in your genes… but in your mindset? In this Wisdom Wednesday episode, Chip Conley reveals the surprising research showing how a simple shift in how we think about aging can add years—yes, actual years—to our lives. From Becca Levy’s longevity findings to Carol Dweck’s growth-mindset principles, Chip breaks down why curiosity, openness, and lifelong learnin...

What if everything you’ve believed about midlife is completely outdated? In this powerful conversation, Marianne Williamson sheds light on the truth about aging, visibility, and what it truly means to enter the second half of life with purpose. She shares raw reflections on menopause, identity shifts, modern rites of passage, and why midlife is less a crisis and more a spiritual turning point. Mar...

What if living to 100 is more realistic than you think? Longevity expert Dan Buettner breaks down the real habits behind the world’s longest-living people, from food and movement to purpose, community, and stress relief. He explains why Americans age faster, what actually adds years to your life, and how simple daily choices can transform your future health. A simple, science-backed path to your b...

What if midlife is actually the start of your happiest years? In this episode, Chip Conley and Derek Gehl break down why life often gets better after 50, from rising emotional intelligence and deeper wisdom to feeling more like your true self. Chip explains why “growing whole” matters more than “staying young,” how Carl Jung’s insights can reshape your mindset, and why a pro-aging outlook can chan...

What happens when Don Lemon gets truly unfiltered? In this heartfelt, funny, and deeply honest conversation, Don opens up about aging with confidence, coming out in midlife, letting go of old shame, and the freedom that comes from no longer needing anyone’s approval. We talk about identity, love, sex, wisdom, and why his mantra “old people be knowing” captures the real gift of growing older. Don a...

Grief isn’t just an emotion, it’s energy that lives in the body until we face it. I sit down with Meghan Jarvis, a trauma therapist and grief mentor who’s helped countless people find their way through loss. Meghan shares her own story of heartbreak, how grief and trauma intertwine, and the six simple practices she teaches to move that heavy energy through the body and back toward healing. We also...

What if everything you’ve believed about aging and retirement is wrong? In this week’s Wisdom Wednesday, Chip and Derek dive into the surprising truth about aging. Why retirement often makes us less healthy, how community and purpose keep us alive longer, and why our “crystallized intelligence” actually gets stronger well into our 60s and 70s. They explore the real ingredients of a meaningful midl...

Ever wonder if slowing down might actually wake you up? In this episode, I sit down with Susan Cain, the bestselling author of Quiet and Bittersweet, to talk about the hidden strengths of introverts, the surprising beauty in melancholy, and why midlife can be the most creative and peaceful chapter of your life. We dig into what it really means to live with depth, authenticity, and joy, without the...

What happens when two New York City professionals lose their jobs, move to a tiny rural town, and accidentally build one of America’s most beloved skincare brands? Brent and Josh of Beekman 1802 reveal how kindness, community, and old-fashioned wisdom became the backbone of their business and their midlife reinvention. They share how loving your neighbor can be a real strategy, why contentment mat...